diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 06c2808a393..918da100936 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -554,6 +554,7 @@ import {
     isImportOrExportSpecifier,
     isImportSpecifier,
     isImportTypeNode,
+    isInCompoundLikeAssignment,
     isIndexedAccessTypeNode,
     isInExpressionContext,
     isInfinityOrNaNString,
@@ -26729,10 +26730,11 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                     const assignedType = getWidenedLiteralType(getInitialOrAssignedType(flow));
                     return isTypeAssignableTo(assignedType, declaredType) ? assignedType : anyArrayType;
                 }
-                if (declaredType.flags & TypeFlags.Union) {
-                    return getAssignmentReducedType(declaredType as UnionType, getInitialOrAssignedType(flow));
+                const t = isInCompoundLikeAssignment(node) ? getBaseTypeOfLiteralType(declaredType) : declaredType;
+                if (t.flags & TypeFlags.Union) {
+                    return getAssignmentReducedType(t as UnionType, getInitialOrAssignedType(flow));
                 }
-                return declaredType;
+                return t;
             }
             // We didn't have a direct match. However, if the reference is a dotted name, this
             // may be an assignment to a left hand part of the reference. For example, for a
@@ -28079,7 +28081,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         // entities we simply return the declared type.
         if (localOrExportSymbol.flags & SymbolFlags.Variable) {
             if (assignmentKind === AssignmentKind.Definite) {
-                return type;
+                return isInCompoundLikeAssignment(node) ? getBaseTypeOfLiteralType(type) : type;
             }
         }
         else if (isAlias) {
diff --git a/src/compiler/factory/utilities.ts b/src/compiler/factory/utilities.ts
index 3aa6f5e6548..221d4874d52 100644
--- a/src/compiler/factory/utilities.ts
+++ b/src/compiler/factory/utilities.ts
@@ -1222,7 +1222,8 @@ function isShiftOperator(kind: SyntaxKind): kind is ShiftOperator {
         || kind === SyntaxKind.GreaterThanGreaterThanGreaterThanToken;
 }
 
-function isShiftOperatorOrHigher(kind: SyntaxKind): kind is ShiftOperatorOrHigher {
+/** @internal */
+export function isShiftOperatorOrHigher(kind: SyntaxKind): kind is ShiftOperatorOrHigher {
     return isShiftOperator(kind)
         || isAdditiveOperatorOrHigher(kind);
 }
diff --git a/src/compiler/utilities.ts b/src/compiler/utilities.ts
index 4eb8cc9d52a..f00b10dbc7b 100644
--- a/src/compiler/utilities.ts
+++ b/src/compiler/utilities.ts
@@ -152,8 +152,6 @@ import {
     forEachChild,
     forEachChildRecursively,
     ForInOrOfStatement,
-    ForInStatement,
-    ForOfStatement,
     ForStatement,
     FunctionBody,
     FunctionDeclaration,
@@ -331,6 +329,7 @@ import {
     isQualifiedName,
     isRootedDiskPath,
     isSetAccessorDeclaration,
+    isShiftOperatorOrHigher,
     isShorthandPropertyAssignment,
     isSourceFile,
     isString,
@@ -3418,9 +3417,9 @@ export function isInExpressionContext(node: Node): boolean {
                 forStatement.incrementor === node;
         case SyntaxKind.ForInStatement:
         case SyntaxKind.ForOfStatement:
-            const forInStatement = parent as ForInStatement | ForOfStatement;
-            return (forInStatement.initializer === node && forInStatement.initializer.kind !== SyntaxKind.VariableDeclarationList) ||
-                forInStatement.expression === node;
+            const forInOrOfStatement = parent as ForInOrOfStatement;
+            return (forInOrOfStatement.initializer === node && forInOrOfStatement.initializer.kind !== SyntaxKind.VariableDeclarationList) ||
+                forInOrOfStatement.expression === node;
         case SyntaxKind.TypeAssertionExpression:
         case SyntaxKind.AsExpression:
             return node === (parent as AssertionExpression).expression;
@@ -4468,23 +4467,29 @@ export const enum AssignmentKind {
     None, Definite, Compound
 }
 
-/** @internal */
-export function getAssignmentTargetKind(node: Node): AssignmentKind {
+type AssignmentTarget =
+    | BinaryExpression
+    | PrefixUnaryExpression
+    | PostfixUnaryExpression
+    | ForInOrOfStatement;
+
+function getAssignmentTarget(node: Node): AssignmentTarget | undefined {
     let parent = node.parent;
     while (true) {
         switch (parent.kind) {
             case SyntaxKind.BinaryExpression:
-                const binaryOperator = (parent as BinaryExpression).operatorToken.kind;
-                return isAssignmentOperator(binaryOperator) && (parent as BinaryExpression).left === node ?
-                    binaryOperator === SyntaxKind.EqualsToken || isLogicalOrCoalescingAssignmentOperator(binaryOperator) ? AssignmentKind.Definite : AssignmentKind.Compound :
-                    AssignmentKind.None;
+                const binaryExpression = parent as BinaryExpression;
+                const binaryOperator = binaryExpression.operatorToken.kind;
+                return isAssignmentOperator(binaryOperator) && binaryExpression.left === node ? binaryExpression : undefined;
             case SyntaxKind.PrefixUnaryExpression:
             case SyntaxKind.PostfixUnaryExpression:
-                const unaryOperator = (parent as PrefixUnaryExpression | PostfixUnaryExpression).operator;
-                return unaryOperator === SyntaxKind.PlusPlusToken || unaryOperator === SyntaxKind.MinusMinusToken ? AssignmentKind.Compound : AssignmentKind.None;
+                const unaryExpression = (parent as PrefixUnaryExpression | PostfixUnaryExpression);
+                const unaryOperator = unaryExpression.operator;
+                return unaryOperator === SyntaxKind.PlusPlusToken || unaryOperator === SyntaxKind.MinusMinusToken ? unaryExpression : undefined;
             case SyntaxKind.ForInStatement:
             case SyntaxKind.ForOfStatement:
-                return (parent as ForInOrOfStatement).initializer === node ? AssignmentKind.Definite : AssignmentKind.None;
+                const forInOrOfStatement = parent as ForInOrOfStatement;
+                return forInOrOfStatement.initializer === node ? forInOrOfStatement : undefined;
             case SyntaxKind.ParenthesizedExpression:
             case SyntaxKind.ArrayLiteralExpression:
             case SyntaxKind.SpreadElement:
@@ -4496,30 +4501,62 @@ export function getAssignmentTargetKind(node: Node): AssignmentKind {
                 break;
             case SyntaxKind.ShorthandPropertyAssignment:
                 if ((parent as ShorthandPropertyAssignment).name !== node) {
-                    return AssignmentKind.None;
+                    return undefined;
                 }
                 node = parent.parent;
                 break;
             case SyntaxKind.PropertyAssignment:
-                if ((parent as ShorthandPropertyAssignment).name === node) {
-                    return AssignmentKind.None;
+                if ((parent as PropertyAssignment).name === node) {
+                    return undefined;
                 }
                 node = parent.parent;
                 break;
             default:
-                return AssignmentKind.None;
+                return undefined;
         }
         parent = node.parent;
     }
 }
 
+/** @internal */
+export function getAssignmentTargetKind(node: Node): AssignmentKind {
+    const target = getAssignmentTarget(node);
+    if (!target) {
+        return AssignmentKind.None;
+    }
+    switch (target.kind) {
+        case SyntaxKind.BinaryExpression:
+            const binaryOperator = target.operatorToken.kind;
+            return binaryOperator === SyntaxKind.EqualsToken || isLogicalOrCoalescingAssignmentOperator(binaryOperator) ?
+                AssignmentKind.Definite :
+                AssignmentKind.Compound;
+        case SyntaxKind.PrefixUnaryExpression:
+        case SyntaxKind.PostfixUnaryExpression:
+            return AssignmentKind.Compound;
+        case SyntaxKind.ForInStatement:
+        case SyntaxKind.ForOfStatement:
+            return AssignmentKind.Definite;
+    }
+}
+
 // A node is an assignment target if it is on the left hand side of an '=' token, if it is parented by a property
 // assignment in an object literal that is an assignment target, or if it is parented by an array literal that is
 // an assignment target. Examples include 'a = xxx', '{ p: a } = xxx', '[{ a }] = xxx'.
 // (Note that `p` is not a target in the above examples, only `a`.)
 /** @internal */
 export function isAssignmentTarget(node: Node): boolean {
-    return getAssignmentTargetKind(node) !== AssignmentKind.None;
+    return !!getAssignmentTarget(node);
+}
+
+function isCompoundLikeAssignment(assignment: AssignmentExpression<EqualsToken>): boolean {
+    const right = skipParentheses(assignment.right);
+    return right.kind === SyntaxKind.BinaryExpression && isShiftOperatorOrHigher((right as BinaryExpression).operatorToken.kind);
+}
+
+/** @internal */
+export function isInCompoundLikeAssignment(node: Node): boolean {
+    const target = getAssignmentTarget(node);
+    return !!target && isAssignmentExpression(target, /*excludeCompoundAssignment*/ true) && isCompoundLikeAssignment(target);
 }
 
 /** @internal */
@@ -4534,8 +4571,7 @@ export type NodeWithPossibleHoistedDeclaration =
     | DefaultClause
     | LabeledStatement
     | ForStatement
-    | ForInStatement
-    | ForOfStatement
+    | ForInOrOfStatement
     | DoStatement
     | WhileStatement
     | TryStatement
diff --git a/tests/baselines/reference/literalWideningWithCompoundLikeAssignments.symbols b/tests/baselines/reference/literalWideningWithCompoundLikeAssignments.symbols
new file mode 100644
index 00000000000..599027e35ff
--- /dev/null
+++ b/tests/baselines/reference/literalWideningWithCompoundLikeAssignments.symbols
@@ -0,0 +1,135 @@
+//// [tests/cases/compiler/literalWideningWithCompoundLikeAssignments.ts] ////
+
+=== literalWideningWithCompoundLikeAssignments.ts ===
+// repro from #13865
+
+const empty: "" = "";
+>empty : Symbol(empty, Decl(literalWideningWithCompoundLikeAssignments.ts, 2, 5))
+
+let foo = empty;
+>foo : Symbol(foo, Decl(literalWideningWithCompoundLikeAssignments.ts, 3, 3))
+>empty : Symbol(empty, Decl(literalWideningWithCompoundLikeAssignments.ts, 2, 5))
+
+foo = foo + "bar"
+>foo : Symbol(foo, Decl(literalWideningWithCompoundLikeAssignments.ts, 3, 3))
+>foo : Symbol(foo, Decl(literalWideningWithCompoundLikeAssignments.ts, 3, 3))
+
+foo // string
+>foo : Symbol(foo, Decl(literalWideningWithCompoundLikeAssignments.ts, 3, 3))
+
+declare const numLiteral: 0;
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+let t1 = numLiteral;
+>t1 : Symbol(t1, Decl(literalWideningWithCompoundLikeAssignments.ts, 9, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t1 = t1 + 42
+>t1 : Symbol(t1, Decl(literalWideningWithCompoundLikeAssignments.ts, 9, 3))
+>t1 : Symbol(t1, Decl(literalWideningWithCompoundLikeAssignments.ts, 9, 3))
+
+t1 // number
+>t1 : Symbol(t1, Decl(literalWideningWithCompoundLikeAssignments.ts, 9, 3))
+
+let t2 = numLiteral;
+>t2 : Symbol(t2, Decl(literalWideningWithCompoundLikeAssignments.ts, 13, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t2 = t2 - 42
+>t2 : Symbol(t2, Decl(literalWideningWithCompoundLikeAssignments.ts, 13, 3))
+>t2 : Symbol(t2, Decl(literalWideningWithCompoundLikeAssignments.ts, 13, 3))
+
+t2 // number
+>t2 : Symbol(t2, Decl(literalWideningWithCompoundLikeAssignments.ts, 13, 3))
+
+let t3 = numLiteral;
+>t3 : Symbol(t3, Decl(literalWideningWithCompoundLikeAssignments.ts, 17, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t3 = t3 * 42
+>t3 : Symbol(t3, Decl(literalWideningWithCompoundLikeAssignments.ts, 17, 3))
+>t3 : Symbol(t3, Decl(literalWideningWithCompoundLikeAssignments.ts, 17, 3))
+
+t3 // number
+>t3 : Symbol(t3, Decl(literalWideningWithCompoundLikeAssignments.ts, 17, 3))
+
+let t4 = numLiteral;
+>t4 : Symbol(t4, Decl(literalWideningWithCompoundLikeAssignments.ts, 21, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t4 = t4 ** 42
+>t4 : Symbol(t4, Decl(literalWideningWithCompoundLikeAssignments.ts, 21, 3))
+>t4 : Symbol(t4, Decl(literalWideningWithCompoundLikeAssignments.ts, 21, 3))
+
+t4 // number
+>t4 : Symbol(t4, Decl(literalWideningWithCompoundLikeAssignments.ts, 21, 3))
+
+let t5 = numLiteral;
+>t5 : Symbol(t5, Decl(literalWideningWithCompoundLikeAssignments.ts, 25, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t5 = t5 / 42
+>t5 : Symbol(t5, Decl(literalWideningWithCompoundLikeAssignments.ts, 25, 3))
+>t5 : Symbol(t5, Decl(literalWideningWithCompoundLikeAssignments.ts, 25, 3))
+
+t5 // number
+>t5 : Symbol(t5, Decl(literalWideningWithCompoundLikeAssignments.ts, 25, 3))
+
+let t6 = numLiteral;
+>t6 : Symbol(t6, Decl(literalWideningWithCompoundLikeAssignments.ts, 29, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t6 = t6 % 42
+>t6 : Symbol(t6, Decl(literalWideningWithCompoundLikeAssignments.ts, 29, 3))
+>t6 : Symbol(t6, Decl(literalWideningWithCompoundLikeAssignments.ts, 29, 3))
+
+t6 // number
+>t6 : Symbol(t6, Decl(literalWideningWithCompoundLikeAssignments.ts, 29, 3))
+
+let t7 = numLiteral;
+>t7 : Symbol(t7, Decl(literalWideningWithCompoundLikeAssignments.ts, 33, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t7 = t7 >> 0
+>t7 : Symbol(t7, Decl(literalWideningWithCompoundLikeAssignments.ts, 33, 3))
+>t7 : Symbol(t7, Decl(literalWideningWithCompoundLikeAssignments.ts, 33, 3))
+
+t7 // number
+>t7 : Symbol(t7, Decl(literalWideningWithCompoundLikeAssignments.ts, 33, 3))
+
+let t8 = numLiteral;
+>t8 : Symbol(t8, Decl(literalWideningWithCompoundLikeAssignments.ts, 37, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t8 = t8 >>> 0
+>t8 : Symbol(t8, Decl(literalWideningWithCompoundLikeAssignments.ts, 37, 3))
+>t8 : Symbol(t8, Decl(literalWideningWithCompoundLikeAssignments.ts, 37, 3))
+
+t8 // number
+>t8 : Symbol(t8, Decl(literalWideningWithCompoundLikeAssignments.ts, 37, 3))
+
+let t9 = numLiteral;
+>t9 : Symbol(t9, Decl(literalWideningWithCompoundLikeAssignments.ts, 41, 3))
+>numLiteral : Symbol(numLiteral, Decl(literalWideningWithCompoundLikeAssignments.ts, 7, 13))
+
+t9 = t9 << 0
+>t9 : Symbol(t9, Decl(literalWideningWithCompoundLikeAssignments.ts, 41, 3))
+>t9 : Symbol(t9, Decl(literalWideningWithCompoundLikeAssignments.ts, 41, 3))
+
+t9 // number
+>t9 : Symbol(t9, Decl(literalWideningWithCompoundLikeAssignments.ts, 41, 3))
+
+declare const literalUnion: "a" | 0;
+>literalUnion : Symbol(literalUnion, Decl(literalWideningWithCompoundLikeAssignments.ts, 45, 13))
+
+let t10 = literalUnion;
+>t10 : Symbol(t10, Decl(literalWideningWithCompoundLikeAssignments.ts, 46, 3))
+>literalUnion : Symbol(literalUnion, Decl(literalWideningWithCompoundLikeAssignments.ts, 45, 13))
+
+t10 = t10 + 'b'
+>t10 : Symbol(t10, Decl(literalWideningWithCompoundLikeAssignments.ts, 46, 3))
+>t10 : Symbol(t10, Decl(literalWideningWithCompoundLikeAssignments.ts, 46, 3))
+
+t10 // string
+>t10 : Symbol(t10, Decl(literalWideningWithCompoundLikeAssignments.ts, 46, 3))
+
diff --git a/tests/baselines/reference/literalWideningWithCompoundLikeAssignments.types b/tests/baselines/reference/literalWideningWithCompoundLikeAssignments.types
new file mode 100644
index 00000000000..b605622a24b
--- /dev/null
+++ b/tests/baselines/reference/literalWideningWithCompoundLikeAssignments.types
@@ -0,0 +1,169 @@
+//// [tests/cases/compiler/literalWideningWithCompoundLikeAssignments.ts] ////
+
+=== literalWideningWithCompoundLikeAssignments.ts ===
+// repro from #13865
+
+const empty: "" = "";
+>empty : ""
+>"" : ""
+
+let foo = empty;
+>foo : ""
+>empty : ""
+
+foo = foo + "bar"
+>foo = foo + "bar" : string
+>foo : string
+>foo + "bar" : string
+>foo : ""
+>"bar" : "bar"
+
+foo // string
+>foo : string
+
+declare const numLiteral: 0;
+>numLiteral : 0
+
+let t1 = numLiteral;
+>t1 : 0
+>numLiteral : 0
+
+t1 = t1 + 42
+>t1 = t1 + 42 : number
+>t1 : number
+>t1 + 42 : number
+>t1 : 0
+>42 : 42
+
+t1 // number
+>t1 : number
+
+let t2 = numLiteral;
+>t2 : 0
+>numLiteral : 0
+
+t2 = t2 - 42
+>t2 = t2 - 42 : number
+>t2 : number
+>t2 - 42 : number
+>t2 : 0
+>42 : 42
+
+t2 // number
+>t2 : number
+
+let t3 = numLiteral;
+>t3 : 0
+>numLiteral : 0
+
+t3 = t3 * 42
+>t3 = t3 * 42 : number
+>t3 : number
+>t3 * 42 : number
+>t3 : 0
+>42 : 42
+
+t3 // number
+>t3 : number
+
+let t4 = numLiteral;
+>t4 : 0
+>numLiteral : 0
+
+t4 = t4 ** 42
+>t4 = t4 ** 42 : number
+>t4 : number
+>t4 ** 42 : number
+>t4 : 0
+>42 : 42
+
+t4 // number
+>t4 : number
+
+let t5 = numLiteral;
+>t5 : 0
+>numLiteral : 0
+
+t5 = t5 / 42
+>t5 = t5 / 42 : number
+>t5 : number
+>t5 / 42 : number
+>t5 : 0
+>42 : 42
+
+t5 // number
+>t5 : number
+
+let t6 = numLiteral;
+>t6 : 0
+>numLiteral : 0
+
+t6 = t6 % 42
+>t6 = t6 % 42 : number
+>t6 : number
+>t6 % 42 : number
+>t6 : 0
+>42 : 42
+
+t6 // number
+>t6 : number
+
+let t7 = numLiteral;
+>t7 : 0
+>numLiteral : 0
+
+t7 = t7 >> 0
+>t7 = t7 >> 0 : number
+>t7 : number
+>t7 >> 0 : number
+>t7 : 0
+>0 : 0
+
+t7 // number
+>t7 : number
+
+let t8 = numLiteral;
+>t8 : 0
+>numLiteral : 0
+
+t8 = t8 >>> 0
+>t8 = t8 >>> 0 : number
+>t8 : number
+>t8 >>> 0 : number
+>t8 : 0
+>0 : 0
+
+t8 // number
+>t8 : number
+
+let t9 = numLiteral;
+>t9 : 0
+>numLiteral : 0
+
+t9 = t9 << 0
+>t9 = t9 << 0 : number
+>t9 : number
+>t9 << 0 : number
+>t9 : 0
+>0 : 0
+
+t9 // number
+>t9 : number
+
+declare const literalUnion: "a" | 0;
+>literalUnion : 0 | "a"
+
+let t10 = literalUnion;
+>t10 : 0 | "a"
+>literalUnion : 0 | "a"
+
+t10 = t10 + 'b'
+>t10 = t10 + 'b' : string
+>t10 : string | number
+>t10 + 'b' : string
+>t10 : 0 | "a"
+>'b' : "b"
+
+t10 // string
+>t10 : string
+
diff --git a/tests/cases/compiler/literalWideningWithCompoundLikeAssignments.ts b/tests/cases/compiler/literalWideningWithCompoundLikeAssignments.ts
new file mode 100644
index 00000000000..e61b19c2280
--- /dev/null
+++ b/tests/cases/compiler/literalWideningWithCompoundLikeAssignments.ts
@@ -0,0 +1,52 @@
+// @strict: true
+// @noEmit: true
+
+// repro from #13865
+
+const empty: "" = "";
+let foo = empty;
+foo = foo + "bar"
+foo // string
+
+declare const numLiteral: 0;
+
+let t1 = numLiteral;
+t1 = t1 + 42
+t1 // number
+
+let t2 = numLiteral;
+t2 = t2 - 42
+t2 // number
+
+let t3 = numLiteral;
+t3 = t3 * 42
+t3 // number
+
+let t4 = numLiteral;
+t4 = t4 ** 42
+t4 // number
+
+let t5 = numLiteral;
+t5 = t5 / 42
+t5 // number
+
+let t6 = numLiteral;
+t6 = t6 % 42
+t6 // number
+
+let t7 = numLiteral;
+t7 = t7 >> 0
+t7 // number
+
+let t8 = numLiteral;
+t8 = t8 >>> 0
+t8 // number
+
+let t9 = numLiteral;
+t9 = t9 << 0
+t9 // number
+
+declare const literalUnion: "a" | 0;
+let t10 = literalUnion;
+t10 = t10 + 'b'
+t10 // string